Email what I want and Decemberween Short Shorts — A picture of Coach Z as an adult with his afro appears on an ornament dated 1974. Given that both of these toons were released in 2006, this could make him at least 50 years old at that time.

Email slumber party — Coach Z is among the "older kids" (himself, Bubs, and the King of Town).

Happy Dethemberween — Coach Z says that in his day "it was 8-tracks" that were put into his slippers by the Decemberween Thnikkaman, rather than blank cassettes and CDs. The heyday of the 8-track was from the late '60s to mid '70s.

Email rated — Coach Z is too young to get into a RRR-rated movie; this makes him no older than sixty at the time of that email.

Email do over — After Strong Mad mistakes Homestar Runner (dressed as The Cheat) for the real The Cheat, Strong Bad tells him that it's "Homestar, from school". This implies that the three are close enough in age to have gone to school together, but Homestar (after returning to pretending to be The Cheat) contests this.

Email senior prom — Homestar is apparently young enough to be a participant in what is supposedly a high school prom.

Strong Bad often refers to doing things in 1987, such as checking what Japanese cartoons are called (TrogdorCon '97) and meeting Van Mundegaarde (2 years), so he was presumably born some time before this. A photograph of Strong Bad circa 1987 (seen in no loafing) shows him in his adult form, rather than his child form.

Cool Things (Easter egg) — Strong Bad says that "[someone The Cheat found in their "death hole"] moved away after the fifth grade", which implies that he is old enough to have passed the fifth grade.

Email coloring — Strong Bad says that he was a "youth" in 1989 when Limozeen was on tour.

Email looking old — Strong Bad attempts to stay relevant to a younger audience. When he says he is going to "relate to some 18-24 year olds", he goes to Strong Sad. Since they were kids at the same time, Strong Bad would presumably be around this age. However, Strong Bad also implies that people in this age range are "at least 10 years younger".

Email diorama — Strong Bad is demonstrating how to create "middle-school appropriate" dioramas, and mentions he made some based on made-up books prior to the advent of the internet, which made prominent growth in 1996; this would imply that Strong Bad was out of middle school (over 14 or 15) by that year, making him at least 37 years old.

Email winter pool — Strong Bad is called a "young'un" by Bubs, implying he is much younger.

Blubb-O's Commercial — Strong Bad refers to himself as "being a young person" for the purposes of the commercial.

Email rated — Strong Bad is too young to get into a RRR-rated movie; this makes him no older than sixty.

Email licensed — One requirement for becoming a licensed unlicensed Strong Bad and The Cheat knock-off seller is that the country of manufacture "changed name five times since [Strong Bad] was in seventh grade".

In Issue 3, Strong Bad states that the Teen Girl Squad are between the ages of 13 and 19.

In Issue 5, Cheerleader claims that they are in college, while So and So claims that they are in 8th grade. It is implied that Cheerleader is lying.

In Issue 9, What's Her Face claims to have had her driver's license for over a year. Given that American teenagers usually get their license around age 16, this would put What's Her Face around the age of 17.